Just outside the heart of the downtown action, the West Loop is an odd blend of blue and white collar. Lords and ladies of Chicago business occupy the high- and mid-rises along the river, while a large number of artists and nine-to-fivers populate the neighborhood's western side.

The West Loop hosts several major attractions, including the United Center, playground of the Chicago Bulls and Blackhawks, and Union Park, home of the annual Pitchfork Music Festival. This is where Oprah Winfrey fans can pilgrimage to her headquarters, Harpo Studios. Local history buffs may be more impressed by the still-thriving Maxwell Street Market, a sprawling outdoor bazaar that dates back more than a century. The city's famous Greek Town area is here as well, the go-to spot for fans of Mediterranean cuisine and music.